


The Darling of the Upper East Side

by starsshines



Category: Gossip Girl (TV 2007)
Genre: Angst and Hurt/Comfort, Drama, Eventual Romance, F/M, Friends to Lovers, Multi, POV Third Person Limited, The main character is black, modern day platforms like instagram and twitter in place of gg's blog, most of the gg characters are minor sorry peeps except carter of course, there is black elite so lets show them, well one of them at least, will add more tags as needed
Language: English
Status: Completed
Published: 2020-04-08
Updated: 2020-04-23
Packaged: 2021-03-02 00:53:37
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,924
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23536345
Author URL: https://archiveofourown.org/users/starsshines/pseuds/starsshines
Summary: Delilah Ryder, back from a somewhat holistic stint in the Deep South, has a lot to learn about the Upper East side once again. For one, you can't go unnoticed from the eyes of the elite and the one and only Gossip Girl.But there are things that Delilah is determined to hide from her old friends and enemies about why she left in the first place.Luckily for her, she's not the only one back in town.
Relationships: Carter Baizen/Delilah Ryder, Carter Baizen/Original Character(s), Carter Baizen/Original Female Character(s), Carter Baizen/Original Female Character(s) of Color
Comments: 1
Kudos: 9





	1. Prologue

**Author's Note:**

> So, hi everyone! Thank you for taking the time to even look at this story. It's an idea I've been sitting on for quite some time and with the reboot of Gossip Girl coming soon, I thought why not? I'm a little nervous to share this as I've never really written quite that much in the third person point of view, limited or omniscient, so please be gentle and enjoy! 
> 
> Another note is that the main character is BLACK, of course the core show didn't have that much representation to begin with so all my original characters or a majority in this story will be POC. 
> 
> For now, I'll give you guys a little to sink your teeth into. Enjoy.

Delilah never meant for it to happen, not like this. But if given the chance, there's no way she'd ever take it all back. All of it. Not a single thing. 

There was a pull almost as natural and strong as the moon on the tides, and when she was with him she was happy in the warmth of his reflected light.

If he had any sense of his collective charm, he never showed it. So self-assured by nature that it never occurred that maybe his perfection in her eyes was predetermined by forces not well understood. How she had to come to love him with a fierceness she didn't know possible, she still wasn't sure. Only months had passed since her almost fateful return to the Upper East Side and so much had happened. It amazed her, how all this revealed how fragile and how full of life as a flute of champagne she could be, teetering on the edge of a table at any moment. 

They say there is nothing quite like love, but they have little to say about someone loving you through your own pain. How strong you had to be, but somehow he did it.

And to think, all of this began only days after her return.

THE BEGINNING


	2. The Beginning

**Summary for the Chapter:**

> Delilah's return to the Upper East Side brings some happy reunions and some unexpected ones. But what could that possibly mean for her going forward? Maybe her return isn't as pleasant as she thought it'd be.

#### 

THE BEGINNING

#### 

CUT TO:

Columbia, Tennessee

Checking her watch, Delilah walked back to the front door. 

It was already past noon, and she’d promised herself that she would get away from this place as soon as she could. Before her more emotional part of her brain decided to just toss all her belongings back into the big, empty house. 

What else could her family possibly be doing to take so long? Weren’t they trying to get her out of here anyways? 

Of course, Delilah fought tooth and nail to stay here but despite her pleading, her darling parents didn’t listen. Why bring her back to the place she was determined to stay away from? She just couldn’t understand. Delilah Ryder was born into one of the richest families in the country and had logged more hours of her life being surrounded by New York City’s elite, and even the poorest person could agree: they sucked. 

_“It’s a change in pace, sweetheart,”_ Her mother would reason, _“Besides, won’t it be so nice to see all your old friends again?”_

That earned her mother an eyebrow raise. Delilah had her reasons for packing her bags and heading with her grandmother out into ‘hick’ country as her mother once put it. That was four years ago and now college seemed to be calling her name. 

Columbia College, that is. And there was no getting out of this. 

Just as Delilah stepped foot inside the entryway, all her family members seemed to file out from the living room. Violet, her youngest sister, was more electrically alive than she remembered. Constance seems to have invigorated a love of drama in her, that’s for sure. 

“I can’t wait for you to see your place in the city! You’re gonna love it!” she said, practically holding herself back from jumping around. Delilah forced a smile for her sake, but couldn’t hide her irritation when her parents appeared at her side. 

For the majority of the ride to the airport, Violet filled the awkward silence with senseless chatter. It was a blessing in disguise, since Delilah’s parents sought to continuously engage with Violet rather than focus their attention on her. The scenery passed by the car in a blur and Delilah was happy to watch it go by. Thinking about how drastically she had changed, how being out here with her grandmother had changed her. 

Now she had to return, a twenty two year old who needed to pick up the pieces of her life. A life, unfortunately, that was back in the Upper East Side. 

\------  


#### 

CUT TO:

New York City, New York

There was no one quite like Brandy Randolph. She lived her entire life in New York, and knows anything there is to know about NYC’s elite even before Gossip Girl. It usually made Delilah speculate whether Brandy was Gossip Girl or not, but alas she wasn’t. Not even ten minutes into arriving in the city that never sleeps did Delilah’s phone rattle with notifications upon notifications. 

Guess she could never exactly hide from Gossip Girl.

**@GossipGirl:** _Hey Upper East Siders. Gossip Girl here. And I have the biggest news ever. One of my many sources, sends us this: “Spotted at JFK, bags in hand: Delilah Ryder.” Was it so long ago that our Darling mysteriously disappeared? And just as suddenly, she’s back. Don’t believe me? See for yourselves. Lucky for us, my source sent proof. Thanks for the photo._

But that wasn’t the only notification that got her attention. 

********

**Brandy:** _I see you’re back in town. Lunch to catch up?_

********

And here she was, getting off the subway in the West Village to meet an old friend. 

********

Delilah loved the West Village—it always reminded her of an earlier New York, when the city was filled with artists and writers and before that, horses and carriages. Now the streets were dotted with fancy boutiques, sushi joints, and students returning from break, carrying their overstuffed bags from Bed, Bath & Beyond. 

********

Soon, she’d be one of those students. The thought was enough to make her sick. 

********

She turned the corner and saw the blue umbrella of the Promised Land. Otherwise known as Vita’s. 

********

“Lil!” shrieked the curly haired woman as she leaped out her chair. Brandy threw her arms around Delilah as if she hadn’t seen her in years. Oh, wait. She hadn’t. “Oh my God, hi!” she said, jumping up and down on her Louboutins, her curly hair springing back and forth. 

********

“I’ve missed you, Lil!” 

********

“I missed you, too, B,” she said, returning Brandy’s frantic hug as best she could, “And you’re glowing.” 

********

“And you’re not,” Brandy said teasingly, letting her go. “Couple more days back and you’ll be good as new!” Her brown eyes were wide and practically electric, much like Violet. Brandy was more alive than anyone Delilah had ever met. 

********

“Here, have some Vita’s,” Brandy said as they sat down. She pushed an oversized mug of green tea matcha and french toast across the table. “Got your favorite.” 

********

“God, I missed this,” Delilah sighed, digging into the meal before her with no regret. 

********

“Almost as much as you missed your best friend, I hope?” Brandy asked, taking a bite out of her parfait. She always went for the healthier options. 

********

She snapped her hazel eyes shut and sucked in a deep breath, she wanted to sink to the floor. Yes, she had grown over the past few years but she cut off everyone she knew in the process. Which probably was not her smartest idea at the start of her self-imposed exile. 

********

And right now? It was like she was that girl that ran away from her problems. And that’s what she wanted to do...run. 

********

“Look, B, I’m sorry. I should have kept in touch and—don’t give me that look— told you what was going on but it’s still so much.” 

********

“Delilah, stop,” Brandy spoke slowly, as if trying not to raise her voice. “I’ll admit I was super pissed off at first. But—” Brandy paused and took a deep breath, “I get it now.” 

********

Delilah simply stared at her, speechless. She couldn’t form words, her brain still slogging through the sentence Brandy had just uttered. Was this the same Brandy she knew in high school? Delilah always thought that Brandy would sooner shoot herself than forgive someone so easily. After a few moments, she regrouped and spoke.

********

“You’re not planning to murder me or something, are you?” 

********

“We’re in college now. Can’t exactly hold much of a grudge now, can I? I got too much homework to do that anyways!” Brandy changes the subject, pulling out her phone. “Now, how about I catch you up on Gossip Girl?”

********

“Like I have a choice? In case you didn’t notice, I’m the hot button issue today.” 

********

\------

********

Delilah couldn’t remember the last time she had seen the stone cold death glare that Blair Waldorf was able to dish out. And since the Universe loved to laugh at her expense, she was on the receiving end of it today. Apparently her return took away from Blair’s shine. Delilah also had the sneaking suspicion that the girl wanted to know what secrets she could paw for. 

********

Delilah had secrets to hide—plenty of them. But they were not going to slip out her mouth anytime soon. Having spent the last four years covering her tracks, she was not going to let Queen B ruin that within days of her return. 

********

Unfortunately, all of the young elite seemed to be here today and they didn’t hide their obvious gawking and secret snapping of pictures as Delilah stood in the corner of the room. Hoping to avoid the attention only brought her more attention. It was truly a losing game. 

********

It didn’t help that her mother had squeezed her into this god awful dress. She felt more like a Republican’s wife than anything else. Delilah kept telling herself to just grin and bear it for now, only a few of these events and she could hide herself underneath mountains of books at Columbia. 

********

The event was for a new charity that Delilah’s father decided to found. The Charlotte Ryder Foundation. She couldn’t be bothered with the details as her father rattled on at the podium. Practically every word out of his mouth made her roll her eyes. 

********

There was a time that Ezekiel Ryder— or Zeke or E.J. for short— would’ve always made Delilah light up like fireworks on the 4th of July. She was a daddy’s girl as much as she didn’t like to admit it. But with all that had happened, Delilah just couldn’t see herself ever being able to listen to him without thinking about it. 

********

“Darling,” Her father addressed her as he walked away from the podium, a phone already up to his ear. “Your grandmother wants to speak to you.”

********

Her grandmother, Darlene Ryder, adjusted to the move better than expected. Her brownstone on Crosby Street was already decorated as if she’d been there for years while Delilah could barely pick out a couch for her living room. 

********

Darlene was still her number one supporter, even when everyone else seemed to be on a different team. So, she gladly took the phone from her father, stepping out into the hallway.

********

“Dede, sweetheart, how are you?” Darlene’s voice was as smooth and sweet as cake batter being poured into a pan. Delilah could listen to old stories of her family being told to her by Darlene for hours and never grow tired of them, just based on her voice alone. 

********

“I’m alright, how about you? Do you need me to stop by the store for you or anything?” Delilah questioned, hoping that her grandmother was in desperate need of company so she could make her great escape. 

********

“Not today,” her grandmother said, sounds of something rummaging in the background, “I take it back, do you mind stopping by The Palace? It seems I left a bracelet of mine when I last met with Bart.” 

********

“Are you insane?” Delilah could only think of Bart’s son, Chuck Bass, and how much she didn’t want to see him. Once was enough at Constance. Chuck reminded her of a serial killer, smooth in his intentions but creepy all the same. 

********

Her grandmother laughed, as if she told a joke. “Not yet, Dede. Please do this for your poor, old grandmother?” 

********

Delilah lets out a sigh, “Fine.”

********

\---- 

********

As the elevator raced upwards, all Delilah could think about was how much her grandmother owed her for this. She checked the inside of her purse for her phone. Delilah promised Serena—yes, van der Woodsen—that they’d catch up as soon as she could manage. 

********

While Blair was still acting rather haughty since earlier events, Serena was more than happy to see Delilah once more. At least someone was. So, hopefully she could be in and out of here ASAP. Just get the bracelet and get the hell out, she told herself. 

********

But things were never that easy. When the elevator reached the top floor, the doors opened to what can only be described as Chuck Bass’s version of a circus. Women and boys spilled out into the marble-floored hallway but the main event came together in the hotel room. The place still screamed decadence as the golden canvassed frames hung perfectly on the walls, the chandelier still looking like an explosion of crystals hung from a skinny chain above their heads. 

********

The people were too drunk to notice stuff like that, of course. They weren’t too drunk to notice that Delilah had entered their space. The women held confused stares at her while the boys couldn’t hold back their rather...lustful stares. It made Delilah want to squirm but she came here on a mission. 

********

“Delilah Ryder, so the rumors were true,” she looked up to the heavens, preparing herself for what was to come before turning around. 

********

Chuck looked about as disheveled as the others surrounding him but still managed to keep an air about him that Delilah couldn’t quite get. Even though she was a few years older than Chuck, that did not stop him from hitting on her on more than one occasion during her senior year and his year as an eighth grader. 

********

Delilah was sure that pattern would continue. 

********

“In the flesh, Bass,” she took a cautious step forward, hoping that she wouldn’t have to engage with him too long. “Let me not waste your time, I’m grabbing something my grandmother left here and then I’m gone.” She walked away to start her search. 

********

“Why not join the fun? There’s plenty to go around.” Chuck offered her a glass of whatever liquor he indulged in. 

********

“Not interested,” she pushed past without another word, rummaging through different books and crannies to find the bracelet. Besides, she didn’t drink anymore anyways. 

********

“Delilah?” A soft voice spoke from behind her and it made Delilah jolt. She whipped her body around, still midway through digging through a drawer. 

********

“Nate?” In a matter of seconds, she was in his arms in a tight bear hug. “If I’d known you’d be here, I would’ve been a lot happier when I first walked in,” She joked before releasing her grip on him. 

********

Okay, so maybe she didn’t completely cut everyone off while exiled. Nate had always been a family friend but Delilah didn’t grow too close to him until her senior year through her sister. It felt strange cutting him out of her life when everything went down, so they remained in touch. Nate was just about the only bright spot in a place surrounded by black holes. But she would never tell Brandy that or she definitely would murder her. 

********

“What brings you back to all ths?” He asked casually, looking around the room. Then his eyes returned to her. “Happy looks good on you,” he added.

********

“Thanks.” Delilah prayed she didn’t blush, it’d been a while since she received a compliment. “Mind helping me out? I’m desperate to get out of here.”

********

“Anything for you.” 

********

Nate finds the bracelet for Delilah in no time flat. Considering he’s the one who helped hide personal belongings with Chuck before their Lost Weekend began as he explained it to her. As she begins to slip out, Nate tells her one final thing. “You made the right choice in coming back.”

********

Somehow, those words make Delilah feel better. Hopefully, the feeling lasts. 

********

“Well, aren’t you a sight for sore eyes?” 

********

Again, as if the Universe wants to see Delilah suffer, she’s faced with more people she doesn’t want to deal with. 

********

Carter Baizen. While the name didn’t put too much fear in her heart, it was still enough to make her steer clear. Delilah and Carter both graduated the same year, they did run in the same social circles but even then she never really knew him too well. She heard things through others but never anything directly. In fact, Brandy showed her the map that Gossip Girl had kept up while Baizen traveled the world. 

********

Somehow, she envied him. Why hide in one place when you could travel the world? Apparently Delilah hadn’t gotten that fucking idea. Nice going there, idiot. 

********

“I don’t know if I could say the same for you, McConaughey,” Delilah pointed out, deciding to keep it polite. “Got quite the intense look going on there.”

********

“What brings you back into town?”

********

“I could ask you the same thing,” she smirked. 

********

“Fair point. I take it you’re not so much a party girl anymore, are you?” 

********

“Well, if the party consists of late nights spent watching random docs and ice cream, then yes.” Delilah points back to the room, “Unfortunately, they're in short supply of ice cream and fully stocked on stupidity.”

********

“And how is it we barely spoke to each other before this?”

********

“I’ll let you figure that out on your own, I’ve really got to go. It was, uh, interesting to see you, Carter.” She turned abruptly, hoping the elevator would open quicker. As the doors closed, Delilah has the slightest inkling that maybe this isn’t the last time she’s going to see Carter, but she’s not sure when next they could possibly meet again.

********


End file.
